Italy rewards slow travel. In two weeks, you’ll trace Rome’s 2,000-year arc from empire to espresso bar, step into the Florentine rooms where the Renaissance rewired Europe, and slide into Milan’s fast-lane of fashion, design, and aperitivo. Trains stitch these cities together with ease, while day trips unlock vineyards, walled towns, alpine panoramas, and lakefront villages.

Fun facts to prime the senses: Romans still drink from ancient aqueduct-fed fountains; Florence’s Duomo dome is the largest brick dome ever built; Milan’s canals once ferried marble used for the Duomo’s spires. Practical notes for 2025: reserve the Vatican, Galleria Borghese, and “The Last Supper” well in advance; the Pantheon now has a low-cost ticketed entry; churches require covered shoulders and knees; avoid driving into ZTL (limited-traffic) city centers.

Cuisine is a regional language here. In Rome, carbonara is silky with guanciale; Tuscany leans into grilled meats, pecorino, and Sangiovese; Milan offers saffron risotto, veal Milanese, and a ritual of aperitivo. We’ll flag where to sip the best espresso, book-timed museum entries, and which trains to catch—so you can spend more time tasting Italy, not troubleshooting it.

Rome

Rome is a living palimpsest: emperors and popes, baroque fountains and neighborhood trattorie, scooters threading lanes that shadow Roman paving stones. Center your wanderings around the historic core, Trastevere’s ivy-clad lanes, and Testaccio’s honest Roman cooking.

Plan to visit the Colosseum, Roman Forum, Palatine Hill, the Pantheon, Trevi Fountain, Spanish Steps, and the Vatican Museums with St. Peter’s Basilica. Time sunsets on Capitoline Hill or the Pincian Terrace overlooking Piazza del Popolo.

Days 1–5: Ancient splendor, Vatican masterpieces, neighborhood life

• Ancient Rome made vivid: Tackle the Colosseum, Forum, and Palatine with a guide to read the ruins like a story. Reserve timed entries; mornings are cooler and less crowded.
• Vatican day: The Museums, Sistine Chapel, and St. Peter’s reward an early skip-the-line slot. Climb the dome for a mosaic-close city panorama.
• Centro Storico stroll: Connect the Pantheon (now ticketed), Piazza Navona, and Trevi. Stop for gelato between baroque churches.
• Trastevere evening: Medieval lanes, trattorie, and a lively piazza scene—great for an after-dinner amaro.
• Optional deep dives: Galleria Borghese (book ahead), Appian Way cycling to catacombs, Capitoline Museums’ she-wolf and imperial statuary.

Curated Viator experiences in Rome (highly recommended):

• Rome: Colosseum, Roman Forum, and Palatine Hill Guided Tour

  

• Vatican Museums, Sistine Chapel Tour and Basilica Access

  

• Winner 2025 Rome Twilight Trastevere Food Tour by Eating Europe

  

• Rome by Golf Cart Private Tour: Beyond the Landmarks

  

Where to eat and drink in Rome:

• Breakfast/coffee: Sant’Eustachio Il Caffè for wood-roasted espresso; Tazza d’Oro by the Pantheon; Marigold (Ostiense) for sourdough, eggs, and pastries; Pasticceria Regoli (since 1916) for maritozzi cream buns.
• Lunch: Roscioli Salumeria con Cucina for cacio e pepe and a deep wine list; Pizzarium Bonci near the Vatican for creative pizza al taglio; Forno Campo de’ Fiori for hot-from-the-oven pizza bianca.
• Dinner: Armando al Pantheon (book well ahead) for classic Roman pastas; Da Enzo al 29 in Trastevere for amatriciana and artichokes; Flavio al Velavevodetto (Testaccio) for carbonara; Cesare al Casaletto for fried starters and great house wine.
• After-hours: Trastevere’s Piazza Trilussa for people-watching; craft cocktails at Drink Kong (Monti) or Jerry Thomas Speakeasy (reservation often needed).

Where to stay (Rome): Browse apartments on VRBO Rome or hotels on Hotels.com Rome. Specific favorites: Hotel de Russie (elegant, near Piazza del Popolo), Hotel Eden - Dorchester Collection (rooftop views), Rome Cavalieri, A Waldorf Astoria Hotel (pool, hilltop vistas), and The Beehive (friendly budget base near Termini).

Getting in and around: Fly into Rome FCO or CIA—compare fares on Omio flights (to/from Europe). For long-haul options beyond Europe, also check Kiwi.com or Trip.com flights. Inside Rome, walk, use the Metro (A/B/C lines), and official taxis (look for white cabs or use apps). Avoid driving within ZTL zones.

Next stop: High-speed train from Rome to Florence takes ~1.5 hours on Frecciarossa/Frecciargento. Expect €25–60 if booked in advance on Omio trains. Aim for a morning departure of Day 6 to maximize time in Florence.

Florence

Florence is the Renaissance in concentrated form: Brunelleschi’s dome, Botticelli’s Primavera, Michelangelo’s David—and a compact tangle of streets where artisans still hand-tool leather and marbled paper. It’s also your gateway to Tuscan hill towns, farm lunches, and Sangiovese vineyards.

Anchor your days around the Duomo complex, Uffizi Gallery, Accademia, and the Arno’s bridges. Cross to the Oltrarno for quieter lanes, workshops, and sunset from Piazzale Michelangelo or San Miniato al Monte.

Days 6–10: Renaissance icons and Tuscan countryside

• Art and architecture: Reserve the Uffizi (Botticelli, Leonardo, Caravaggio) and the Accademia (Michelangelo’s David). Climb either Brunelleschi’s Dome (narrow, steeper) or Giotto’s Campanile (stairs with views of the dome).
• Oltrarno artisans: Wander Via Maggio and Santo Spirito for woodworkers, goldsmiths, and tiny wine bars. Boboli Gardens offer a Medici-era outdoor museum feel.
• Tuscany day trips: Siena’s shell-shaped Piazza del Campo, San Gimignano’s medieval towers, Pisa’s Leaning Tower—pair culture with a winery lunch or a dedicated wine-tasting half day.

Curated Viator experiences in/around Florence:

• Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

  

• Small-Group Wine Tasting Experience in the Tuscan Countryside

  

Where to eat and drink in Florence:

• Breakfast/coffee: Ditta Artigianale (specialty coffee roaster), Caffè Gilli (historic 1733 salon on Piazza della Repubblica), Pasticceria Nencioni for cornetti and schiacciata.
• Lunch: All’Antico Vinaio for stuffed schiacciata sandwiches; Mercato Centrale’s upstairs food hall—try Da Nerbone’s lampredotto or La Pasta Fresca’s tagliatelle; Il Pizzaiuolo for Neapolitan pies.
• Dinner: Trattoria Sostanza (famous butter chicken and bistecca—book early), Buca Lapi for old-school Florentine steakhouse vibes, Osteria del Cinghiale Bianco in Oltrarno for hearty Tuscan plates.
• Sweet things: Gelateria dei Neri for classic flavors; La Carraia on the Oltrarno side for creamy pistachio and stracciatella.

Where to stay (Florence): See apartment stays on VRBO Florence or hotels on Hotels.com Florence. Top picks include Grand Hotel Minerva (rooftop pool by Santa Maria Novella), Hotel Santa Croce (value in a historic building), Hotel Della Signoria (steps from Ponte Vecchio), and for a splurge, Four Seasons Hotel Firenze.

Next stop: Florence to Milan on a high-speed train takes ~1 hour 45 minutes–2 hours, typically €20–€60 if booked ahead via Omio trains. Morning of Day 11 is ideal; sit on the left side heading north for Apennine views.

Milan

Milan is Italy’s modern engine: couture windows, grand cafés, and a Gothic cathedral that looks like a marble forest. It’s a springboard to Lake Como’s villas and—on the Bernina Red Train—one of Europe’s most dramatic alpine rides.

See the Duomo (rooftop terraces are a must), Galleria Vittorio Emanuele II, Sforza Castle, Brera’s galleries and lanes, and Leonardo’s “Last Supper” in Santa Maria delle Grazie (tickets often sell out weeks ahead).

Days 11–14: Design capital, Lake Como, and the Alps

• Milan highlights: Duomo inside and rooftops, La Scala’s museum, Brera Art Gallery, and time in the Navigli canals at golden hour for aperitivo culture.
• Lake Como day trip: Train to Varenna (about 1:03 from Milano Centrale), ferry to Bellagio and Menaggio, stroll gardens like Villa Melzi (seasonal) and sip a spritz by the water.
• Swiss Alps excursion: Make a full-day Bernina Red Train run to St. Moritz for glaciers, spirals, and stone viaducts—an unforgettable UNESCO-listed railway.

Curated Viator experience from Milan:

• Bernina Red Train, Swiss Alps & St Moritz From Milan

  

Where to eat and drink in Milan:

• Breakfast/coffee: Pavé for pastries and cappuccino; Marchesi 1824 (by Galleria) for a refined coffee-and-pasticcini stop.
• Lunch: Luini for classic panzerotti near the Duomo; De Santis (Corso Magenta) for gourmet toasted panini; Miscusi for fresh pasta if you’re in a hurry.
• Dinner: Trippa (book early) for contemporary takes and Milanese offal, Ratanà (Isola) for risotto alla milanese and cotoletta in a cool former railway building, Piz for a joyful, affordable pizza night.
• Aperitivo/cocktails: Mag Café or Rita in Navigli for artful drinks; Nottingham Forest for creative concoctions with a global reputation.

Where to stay (Milan): Compare options on VRBO Milan or Hotels.com Milan. Excellent choices: Hotel Principe di Savoia (grand classic), Room Mate Giulia (steps from the Duomo), Ostello Bello (top-tier hostel with social vibes), and UNAHOTELS Cusani Milano (between Sforza Castle and Brera).

Getting around and day trips: Milan’s Metro is efficient; buy a 3-day pass if staying central. For Como or Varenna trains, check times and fares on Omio trains (usually €7–€12, ~1 hour). For airport transfers (MXP/LIN/BGY), Malpensa Express to Cadorna/Centrale is convenient.

Logistics at a glance (estimated times and costs)

• Flights in/out: Search fares on Omio flights (to/from Europe). For additional global options, check Kiwi.com and Trip.com flights.
• Rome → Florence: ~1h30 by high-speed train; €25–€60 if booked in advance on Omio trains. Depart morning of Day 6.
• Florence → Milan: ~1h45–2h by high-speed train; €20–€60 via Omio trains. Depart morning of Day 11.
• Florence/Tuscany tours: Full-day countryside tours typically run 10–12 hours; wine-focused half days ~5 hours.
• Milan → Lake Como (Varenna): ~1:03 by regional train; €7–€12 each way on Omio trains. Ferries connect Varenna–Bellagio–Menaggio every 20–40 minutes (seasonal frequency varies).

Insider planning tips

• Reserve ahead: Vatican Museums, Colosseum (with Forum/Palatine), Uffizi, Accademia, Galleria Borghese (Rome), and “The Last Supper” in Milan. Pantheon now requires a small ticket and timed entry; book the earlier slots.
• Dress codes: Shoulders and knees covered for major churches (St. Peter’s, Santa Maria delle Grazie). Carry a light scarf.
• Safety and fees: Beware of pickpockets in tourist zones and on transit. Expect a city tourist tax at hotels, paid on-site in cash or card.
• Hydrate smartly: Rome’s nasoni fountains provide free drinkable water; bring a reusable bottle.
• Seasonality: Peak heat in July–August; book early morning entries and plan siestas. Spring and fall are ideal for this itinerary.

Trip pacing: Days 1–5 Rome for ancient sites, Vatican art, and neighborhood flavor. Days 6–10 Florence for Renaissance icons and Tuscan wine country. Days 11–14 Milan for design, Duomo rooftops, Lake Como, and the Bernina alpine rail journey.

In two weeks you’ll taste Italy’s layers—Roman stones underfoot, Tuscan hills in your glass, alpine air in your lungs—without rushing. With smart train hops, timed tickets, and a few stellar guided tours, this itinerary balances A-list sights with local tables you’ll talk about long after wheels up.